Substituted sulphonylamino(thio)carbonyl compounds

ABSTRACT

The invention relates to novel substituted sulphonylamino(thio)carbonyl compounds of the formula (I)  
                 
 
     in which  
     A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N—, or —N═CH— or —CH═CH—,  
     Q represents oxygen or sulphur,  
     R 1  represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,  
     R 2  represents cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and  
     R 3  represents respectively optionally substituted heterocyclyl having 5 ring members of which at least one represents oxygen, sulphur or nitrogen and a further one to three may represent nitrogen  
     (except for certain individual prior art compounds), furthermore to salts of novel compounds of the formula (I), to various processes and novel intermediates for preparing the novel compounds and to their use as herbicides.

[0001] The invention relates to novel substitutedsulphonylamino(thio)carbonyl compounds, to a plurality of-processes andnovel intermediates for their preparation and to their use asherbicides.

[0002] It is already known that certain sulphonylaminocarbonyl compoundssuch as, for example, the compoundsN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide(cf. EP 569810, Example 204),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide(cf. EP 569810, Example 239),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 278),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 329),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxamide(cf. EP 569810, Example 366),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide(cf. EP 569810, Example 441),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide(cf. EP 569810, Example 532),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide(cf EP 569810, Example 576),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide(cf. EP 569810, Example 607),N-(2-chloro-6-methoxy-carbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide(cf. EP 569810, Example 641),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 701),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 735),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 757),N-(2-chloro-6-methoxy-carbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide(cf. EP 569810, Example 791),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide(cf. EP 569810, Example 861),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide(cf EP 569810, Example 871),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide(cf. EP 569810, Example 918) andN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide(cf. EP 569810, Example 925) have herbicidal properties (cf. also EP341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE4029753). However, the activity of these compounds is not satisfactoryin every respect.

[0003] This invention, accordingly, provides the novel substitutedsulphonylamino(thio)carbonyl compounds of the general formula (I),

[0004] in which

[0005] A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N— or—N═CH—, or —CH═CH—,

[0006] Q represents oxygen or sulphur,

[0007] R¹ represents respectively optionally substituted alkyl, alkenyl,alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl orheterocyclylalkyl,

[0008] R² represents cyano, nitro, halogen or represents respectivelyoptionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl, alkyl-sulphonyl, alkenyl, alkinyl, alkenyloxy oralkinyloxy, and

[0009] R³ represents respectively optionally substituted heterocyclylhaving 5 ring members of which at least one represents oxygen, sulphuror nitrogen and a further one to three may represent nitrogen,

[0010] and salts of compounds of the formula (I),

[0011] except for the prior art compoundsN-(2-chloro-6-methoxycarbonyl-phenyl-sulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide(cf. EP 569810, Example 204),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide(cf. EP 569810, Example 239),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 278),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide(cf EP 569810, Example 329),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxamide(cf. EP 569810, Example 366),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide(cf. EP 569810, Example 441),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide(cf. EP 569810, Example 532),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide(cf. EP 569810, Example 576),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide(cf. EP 569810, Example 607),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide(cf. EP 569810, Example 641),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 701),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide(cf EP 569810, Example 735),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 757),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide(cf. EP 569810, Example 791),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide(cf. EP 569810, Example 861),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide(cf. EP 569810, Example 871),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide(cf. EP 569810, Example 918) andN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide(cf EP 569810, Example 925) which are excluded by disclaimer.

[0012] The novel substituted sulphonylamino(thio)carbonyl compounds ofthe general formula (I), are obtained when

[0013] (a) sulphonamides of the general formula (II)

[0014] in which

[0015] A, R¹ and R² are each as defined above, are reacted with(thio)carboxylic acid derivatives of the general formula (III)

[0016] in which

[0017] Q and R³ are each as defined above and

[0018] Z represents halogen, alkoxy, aryloxy or arylalkoxy,

[0019] if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0020] or when

[0021] (b) sulphonyl iso(thio)cyanates of the general formula (IV)

[0022] in which

[0023] A, Q, R¹ and R² are each as defined above, are reacted withheterocycles of the general formula (V)

H—R³  (V)

[0024] in which

[0025] R³ is as defined above, if appropriate in the presence of areaction auxiliary and if appropriate in the presence of a diluent,

[0026] or when

[0027] (c) sulphonyl chlorides of the general formula (VI)

[0028] in which

[0029] A, R¹ and R² are each as defined above, are reacted withheterocycles of the general formula (V)

H—R³  (V)

[0030] in which

[0031] R³ is as defined above,

[0032] and metal (thio)cyanates of the general formula (VII)

MQCN  (VII)

[0033] in which

[0034] Q is as defined above,

[0035] if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

[0036] or when

[0037] (d) sulphonyl chlorides of the general formula (VI)

[0038] in which

[0039] A, R¹ and R² are each as defined above, are reacted with(thio)carboxamides of the general formula (VIII)

[0040] in which

[0041] Q and R³ are each as defined above,

[0042] if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0043] or when

[0044] (e) sulphonylamino(thio)carbonyl compounds of the general formula(IX)

[0045] in which

[0046] A, Q, R¹ and R² are each as defined above and

[0047] Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reactedwith heterocycles of the general formula (V)

H—R³  (V)

[0048] in which

[0049] R³ is as defined above,

[0050] if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a diluent,

[0051] and the compounds of the formula (I) obtained by processes (a),(b), (c), (d) or (e) are, if desired, converted into salts by customarymethods.

[0052] The novel substituted sulphonylamino(thio)carbonyl compounds ofthe general formula (I) have strong herbicidal activity.

[0053] The invention preferably provides compounds of the formula (I) inwhich

[0054] A represents oxygen, sulphur, NH, N—C₁-C₄-alkyl, N-phenyl, —CH═N—or —N═CH— or —CH═CH—,

[0055] Q represents oxygen or sulphur,

[0056] R¹ represents optionally cyano-, nitro-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₆-alkyl, represents respectively optionallycyano- or halogen-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, representsrespectively optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, represents respectivelyoptionally cyano-, nitro-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl orphenyl-C₁-C₄-alkyl, or represents respectively optionally cyano-,nitro-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted heterocyclyl orheterocyclyl-C₁-C₄-alkyl, where in each case the heterocyclyl group isselected from the group consisting of oxetanyl, thietanyl, furyl,tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl,thiazolyl, oxadiazolyl, thiadiazolyl,

[0057] R² represents cyano, nitro, halogen, represents respectivelyoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl or C₁-C₄-alkylsulphonyl, or represents respectivelyoptionally cyano- or halogen-substituted C₂-C₄-alkenyl, C₂-C₄-alkinyl,C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy, and

[0058] R³ represents respectively optionally substituted heterocyclyl ofthe formulae below,

[0059] in which

[0060] Q¹, Q² and Q³ each represent oxygen or sulphur and

[0061] R⁴ represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylidene-amino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents respectivelyoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents respectively optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonyl-amino, represents C₃-C₆-alkenyloxy, representsdi-(C₁-C₄-alkyl)-amino, represents respectively optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-amino orC₃-C₆-cycloalkyl-C₁-C₄-alkyl, or represents respectively optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl- and/or C₁-C₄-alkoxy-substituted phenyl orphenyl-C₁-C₄-alkyl,

[0062] R⁵ represents hydrogen, hydroxyl, mercapto, amino, cyano,fluorine, chlorine, bromine, iodine, represents optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents respectivelyoptionally fluorine-; chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents respectively optionally fluorine-,chlorine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedC₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonylamino, represents C₃-C₆-alkenyloxy,C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio,C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, representsdi-(C₁-C₄-alkyl)-amino, represents respectively optionally methyl-and/or ethyl-substituted aziridino, pyrrolidino, piperidino ormorpholino, represents respectively optionally fluorine-, chlorine-,bromine-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio orC₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents respectively optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio,phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or

[0063] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to 11 carbon atoms, furthermore

[0064] R⁶, R⁷ and R⁸ are identical or different and each representshydrogen, cyano, fluorine, chlorine, bromine, or represents respectivelyoptionally fluorine-, chlorine-, bromine- or C₁-C₄-alkoxy-substitutedalkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio,alkenylthio, alkinylthio, alkylsulphinyl or alkylsulphonyl having ineach case up to 6 carbon atoms or represent optionally cyano-,fluorine-, chlorine-, bromine- or C₁-C₄-alkyl-substituted cycloalkylhaving 3 to 6 carbon atoms,

[0065] except for the prior art compoundsN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide(cf. EP 569810, Example 204),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide(cf. EP 569810, Example 239),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 278),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 329),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxamide(cf. EP 569810, Example 366),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide(cf. EP 569810, Example 441),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide(cf. EP 569810, Example 532),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide(cf. EP 569810, Example 576),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide(cf. EP 569810, Example 607),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide(cf. EP 569810, Example 641),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 701),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide(cf EP 569810, Example 735),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide(cf EP 569810, Example 757),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide(cf. EP 569810, Example 791),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide(cf. EP 569810, Example 861),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide(cf. EP 569810,

[0066] Example 871),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide(cf. EP 569810, Example 918) andN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide(cf. EP 569810, Example 925) which are excluded by disclaimer.

[0067] The invention furthermore preferably provides the sodium,potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I) in which A, Q, R¹, R² and R³ are eachpreferably as defined above.

[0068] The invention in particular provides compounds of the formula(I), in which

[0069] A represents sulphur, N-methyl, —CH═N— or —N═CH— or —CH═CH—,

[0070] Q represents oxygen or sulphur,

[0071] R¹ represents respectively optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i- or s-butyl, represents respectively optionally cyano-, fluorine-or chlorine-substituted propenyl, butenyl, propinyl or butinyl,represents respectively optionally cyano-, fluorine-, chlorine-, methyl-or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclo-hexylmethyl, represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-,ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,phenylmethyl or phenylethyl, or represents respectively optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, methoxy- orethoxy-substituted heterocyclyl or heterocyclyl-methyl, where in eachcase the heterocyclyl group is selected from the group consisting ofoxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,

[0072] R² represents cyano, fluorine, chlorine, bromine, representsrespectively optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or representsrespectively, optionally cyano-, fluorine- or chlorine-substitutedpropenyl, butenyl, propinyl, butinyl, propenyloxy or propinyloxy, and

[0073] R³ represents respectively optionally substituted heterocyclyl ofthe formulae below,

[0074] in which

[0075] Q¹, Q² and Q³ each represent oxygen or sulphur and

[0076] R⁴ represents hydrogen, hydroxyl, amino, represents respectivelyoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, representsrespectively optionally fluorine-, chlorine- or bromine-substitutedpropenyl, butenyl, propinyl or butinyl, represents respectivelyoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy or butenyloxy, represents dimethylamino or diethylamino,represents respectively optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents respectively optionally fluorine-,chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenylor benzyl,

[0077] R⁵ represents hydrogen, hydroxyl, mercapto, amino, fluorine,chlorine, bromine, represents respectively optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents respectively optionallyfluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl,propinyl or butinyl, represents respectively optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy,butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthiobutenylthio, propinylthio, butinylthio, propenylamino, butenylamino,propinylamino or butinylamino, represents dimethylamino, diethylamino ordipropylamino, represents respectively optionally fluorine-, chlorine-,methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or representsrespectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl-,methoxy- and/or methoxycarbonyl-substituted phenyl, benzyl, phenoxy,benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or

[0078] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to 11 carbon atoms, furthermore

[0079] R⁶, R⁷ and R⁸ are identical or different and each representshydrogen, cyano, fluorine, chlorine, bromine, or represents respectivelyoptionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl,propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- ort-butoxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio,butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, or represents cyclopropyl,

[0080] except for the prior art compoundsN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide(cf EP 569810, Example 204),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide (cfEP 569810, Example 239),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide(cf EP 569810, Example 278),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide(cf. EP 569810, Example 329),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-oxazole-4-carboxamide(cf. EP 569810, Example 366),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide(cf. EP 569810, Example 441),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide(cf. EP 569810, Example 532),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide(cf. EP 569810, Example 576),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide(cf. EP 569810, Example 607),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide(cf. EP 569810, Example 641),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 701),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 735),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide(cf. EP 569810, Example 757),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide(cf. EP 569810, Example 791),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide(cf. EP 569810, Example 861),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide(cf. EP 569810, Example 871),N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-4-carboxamide(cf. EP 569810, Example 918) andN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide(cf. EP 569810, Example 925) which are excluded by disclaimer.

[0081] A very particularly preferred group of compounds according to theinvention are the compounds of the formula (I) in which

[0082] A represents sulphur or —CH═CH—,

[0083] Q represents oxygen or sulphur,

[0084] R¹ represents methyl, ethyl, n- or i-propyl, 2-cyano-ethyl,2-fluoro-ethyl, 2,2-difluoro-ethyl, 2,2,2-trifluoro-ethyl,2-chloro-ethyl, 2,2-dichloro-ethyl, 2,2,2-trichloro-ethyl,2-methoxy-ethyl, 2-ethoxy-ethyl or oxetanyl,

[0085] R² represents fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, n-, i- or s-butyl, trifluoromethyl, methoxy, ethoxy, n- ori-propoxy, difluoromethoxy, trifluoromethoxy or trifluoroethoxy, and

[0086] R³ represents optionally substituted triazolinyl of the formulabelow

[0087] in which

[0088] Q¹ represents oxygen or sulphur and

[0089] R⁴ represents respectively optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, representsrespectively optionally fluorine- or chlorine-subsituted propenyl orpropinyl, represents methoxy, ethoxy, n- or i-propoxy, methylamino,ethylamino, n- or i-propylamino, represents propenyloxy, representsdimethylamino or represents cyclopropyl,

[0090] R⁵ represents chlorine or bromine, represents respectivelyoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, representsrespectively optionally fluorine-, chlorine- or bromine-substitutedethenyl, propenyl, butenyl, propinyl or butinyl, represents respectivelyoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-subsitutedmethoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio,propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino,butenylamino, propinylamino or butinylamino, represents dimethylamino,diethylamino or dipropylamino, represents respectively optionallyfluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio,cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio,cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino orcyclohexylmethylamino, or represents respectively optionally fluorine-,chlorine-, methyl-, trifluoromethyl-, methoxy- and/ormethoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy,phenylthio, benzylthio, phenylamino or benzylamino, or

[0091] R⁴ and R⁵ together represent optionally branched alkanediylhaving 3 to 11 carbon atoms.

[0092] The radical definitions listed above, whether general or listedin ranges of preference, apply both to the end products of the formula(I) and, correspondingly, to the starting materials and/or intermediatesrequired in each case for the preparation. These radical definitions canbe combined as desired with one another, thus including combinationsbetween the preferred ranges indicated.

[0093] Using, for example,2-fluoro-6-methoxycarbonyl-benzenesulphonamide and5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazole-3-thioneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following equation:

[0094] Using, for example, 4-chloro-2-ethoxycarbonyl-3-thienylsulphonylisothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (b)according to the invention can be illustrated by the following equation:

[0095] Using, for example, 2-methoxycarbonyl-6-methyl-benzenesulphonylchloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one andpotassium cyanate as starting materials, the course of the reaction inthe process (c) according to the invention can be illustrated by thefollowing equation:

[0096] Using, for example,2-ethoxycarbonyl-6-trifluoromethyl-benzenesulphonyl chloride and5-methyl-1,2,4-oxadiazole-3-carboxamide as starting materials, thecourse of the reaction in the process (d) according to the invention canbe illustrated by the following equation:

[0097] Using, for example,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-O-methyl-urethane and4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as startingmaterials, the course of the reaction in the process (e) according tothe invention can be illustrated by the following equation:

[0098] A general definition of the sulphonamides to be used as startingmaterials in the process (a) according to the invention for preparingthe compounds of the formula (I) is given by the formula (II). In theformula (II), A, R¹ and R² each preferably or in particular have thatmeaning which has already been indicated above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferable or, respectively, particularly preferablefor A, R¹ and R².

[0099] The starting materials of the formula (II) are known and/or canbe prepared by processes known per se (cf. U.S. Pat. Nos. 4,546,179,5,084,086, 5,157,119, WO 8909214, WO9115478).

[0100] The sulphonamides of the general formula (IIa)

[0101] in which

[0102] R¹ and R² are each as defined above have not yet been disclosedin the literature and, as novel compounds, form part of thesubject-matter of the present application.

[0103] The novels sulphonamides of the formula (IIa) are obtained whensulphonyl chlorides of the formula (VIa)

[0104] in which

[0105] R¹ and R² are each as defined above,

[0106] are reacted with ammonia, if appropriate in the presence of adiluent such as, for example, water, at temperatures between 0° C. and50° C. (cf. the Preparation Examples).

[0107] The sulphonyl chlorides of the formula (VIa) have not yet beendisclosed in the literature; as novel compounds, they also form part ofthe subject-matter of the present application.

[0108] The novel sulphonyl chlorides of the formula (VIa) are obtainedwhen corresponding amino compounds of the general formula (X)

[0109] in which

[0110] R¹ and R² are each as defined above,

[0111] are reacted with an alkali metal nitrite such as, for example,sodium nitrite, in the presence of hydrochloric acid at temperaturesbetween −10° C. and +10° C. and the resulting diazonium salt solution isreacted with sulphur dioxide in the presence of a diluent such as, forexample, dichloromethane, 1,2-dichloro-ethane or acetic acid, and inthe.presence of a catalyst such as, for example, copper(I) chlorideand/or copper(II) chloride, at temperatures between −10° C. and +50° C.(cf. the Preparation Examples).

[0112] The amino compounds of the formula (X) required as intermediatesare known and/or can be prepared by processes known per se (cf. DE3018134, DE 3804794, EP 298542, Preparation Examples).

[0113] A general definition of the (thio)carboxylic acid derivativesfurthermore to be used as starting materials in the process (a)according to the invention for preparing the compounds of the formula(I) is given by the formula (III). In the formula (III), Q and R³ eachpreferably or in particular have that meaning which has already beenindicated above in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred or,respectively, particularly preferred for Q and R³; Z preferablyrepresents fluorine, chlorine, bromine, C₁-C₄-alkoxy, phenoxy orbenzyloxy, in particular chlorine, methoxy, ethoxy or phenoxy.

[0114] The starting materials of the formula (III) are known and/or canbe prepared by processes known per se (cf. EP 459244, EP 341489, EP422469, EP 425948, EP 431291, EP 507171, EP 534266).

[0115] A general definition of the sulphonyl iso(thio)cyanates to beused as starting materials in the process (b) according to the inventionfor preparing the compounds of the formula (I) is given by the formula(IV). In the formula (IV), A, Q, R¹ and R² each preferably or inparticular have that meaning which has already been indicated above inconnection with the description of the compounds of the formula (I)according to the invention as being preferred or, respectively,particularly preferred for A, Q, R¹ and R².

[0116] The starting materials of the formula (IV) are known and/or canbe prepared by processes known per se (cf. EP 46626, U.S. Pat. No.4,701,535, Preparation Examples).

[0117] A general definition of the heterocycles to be used as startingmaterials in the process (b), (c) and (e) according to the invention forpreparing the compounds of the formula (I) is given by the formula (V).In the formula (V), R³ preferably or in particular has that meaningwhich has already been indicated above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred or, respectively, particularly preferredfor R³.

[0118] The starting materials of the formula (V) are known and/or can beprepared by known processes (cf. EP 341489, EP 422469, EP 425948, EP431291, EP 507171, EP 534266).

[0119] A general definition of the sulphonyl chlorides to be used asstarting materials in the processes (c) and (d) according to theinvention for preparing the compounds of the formula (I) is given by theformula (VI). In the formula (VI), A, R¹ and R² each preferably or inparticular have that meaning which has already been indicated above inconnection with the description of the compounds of the formula (I)according to the invention as being preferred or, respectively,particularly preferred for A, R¹ and R².

[0120] The starting materials of the formula (VI) are known and/or canbe prepared by processes known per se (cf. U.S. Pat. Nos. 4,546,179,5,084,086, 5,157,119, WO 8909214, WO 9115478, WO 9213845, PreparationExamples). However, as already mentioned, the compounds of the formula(VI) where A═S, i.e. the compunds of the sub-group of the formula (VIa),are novel.

[0121] A general definition of the (thio)carboxamides to be used asstarting materials in the process (d) according to the invention forpreparing the compounds of the formula (I) is given by the formula(VIII). In the formula (VIII), Q and R³ each preferably or in particularhave that meaning which has already been indicated above in connectionwith the description of the compounds of the formula (I) according tothe invention as being preferred or, respectively, particularlypreferred for Q and R³.

[0122] The starting materials of the formula (VIII) are known and/or canbe prepared by processes known per se (cf. EP 459244).

[0123] A general definition of the sulphonylamino(thio)carbonylcompounds to be used as starting materials in the process (e) accordingto the invention for preparing the compounds of the formula (I) is givenby the formula (IX). In the formula (IX), A, Q, R¹ and R² eachpreferably or in particular have that meaning which has already beenindicated above in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred or,respectively, particularly preferred for A, Q, R¹ and R²; Z preferablyrepresents fluorine, chlorine, bromine, C₁-C₄-alkoxy, phenoxy orbenzyloxy, in particular represents chlorine, methoxy, ethoxy orphenoxy.

[0124] The starting materials of the formula (IX) are known and/or canbe prepared by methods known per se.

[0125] The processes (a), (b), (c), (d) and (e) according to theinvention for the preparation of the novel compounds of the formula (I)are preferably carried out using diluents. Suitable diluents in thiscontext are virtually all inert organic solvents. These include,preferably, aliphatic and aromatic, optionally halogenated hydrocarbonssuch as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine,ligroin, benzene, toluene, xylene, methylene chloride, ethylenechloride, chloroform, tetrachloromethane, chlorobenzene ando-dichlorobenzene; ethers such as diethyl ether and dibutyl ether,glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran anddioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropylketone and methyl isobutyl ketone; esters such as methyl acetate andethyl acetate; nitriles, for example acetonitrile and propionitrile;amides, for example dimethylformamide, dimethylacetamide andN-methylpyrrolidone, and also dimethyl sulphoxide,tetramethylenesulphone and hexamethylphosphorictriamide.

[0126] Suitable reaction auxiliaries and/or acid acceptors for theprocesses (a), (b), (c), (d) and (e) according to the invention are allacid-binding agents which are conventionally used for such reactions.Preference is given to alkali metal hydroxides, such as, for example,sodium hydroxide and potassium hydroxide, alkaline earth metalhydroxides such as, for example, calcium hydroxide, alkali metalcarbonates and alkoxides, such as sodium carbonate and potassiumcarbonate, sodium tert-butoxide and potassium tert-butoxide, and alsobasic nitrogen compounds, such as trimethylamine, triethylamine,tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine,ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine,N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6dimethyl-, 2-ethyl-, 4-ethyl- and5-ethyl-2-methyl-pyridine, 1 ,5-diazabicyclo[4,3,0]-non-5-ene (DBN),1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane(DABCO).

[0127] The reaction temperatures in the processes (a), (b), (c), (d) and(e) according to the invention can be varied within a relatively widerange. The processes are in general carried out at temperatures ofbetween −20° C. and +150° C., preferably at temperatures between 0° C.and +100° C.

[0128] The processes (a), (b), (c), (d) and (e) according to theinvention are generally carried out under atmospheric pressure. However,it is also possible to operate under elevated or reduced pressure.

[0129] For carrying out processes (a), (b), (c), (d) and (e) accordingto the invention, the starting materials required in each case are ingeneral employed in approximately equimolar quantities. However, it isalso possible to use one of the components employed in each case in arelatively large excess. The reactions are in general carried out in asuitable diluent in the presence of an acid acceptor, and the reactionmixture is stirred for a number of hours at the-particulartemperature-required. Work-up in the case of the processes (a), (b),(c), (d) and (e) according to the invention is in each case carried outby customary methods (cf. the Preparation Examples).

[0130] Salts can be prepared, if desired, from the compounds of thegeneral formula (I) according to the invention. Such salts are obtainedin a simple manner by customary methods of forming salts, for example bydissolving or dispersing a compound of the formula (I) in an appropriatesolvent, for example methylene chloride, acetone, tert-butyl methylether or toluene, and adding an appropriate base. The salts can then—ifdesired after prolonged stirring—be isolated by concentration orfiltration with suction.

[0131] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed-killers.By weeds, in the broadest sense, are to be understood all plants whichgrow in locations where they are not wanted. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

[0132] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0133] Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

[0134] Dicotyledonous cultures of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

[0135] Monocolyledonous weeds of the genera: Echinochloa, Setaria,Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium,Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria,Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

[0136] Monocotyledonous cultures of the genera: Oryza, Zea, Triticum,Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagusand Allium.

[0137] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0138] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial crops, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, inlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

[0139] The compounds of the formula (I) according to the invention areparticularly suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledenous and dicotyledenous crops, bothpre-emergence and post-emergence.

[0140] To some extent, the compounds of the formula (I) also havefungicidal activity, for example against Pyricularia oryzae on rice.

[0141] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic materials impregnatedwith active compound, and very fine capsules in polymeric substances.

[0142] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam formers.

[0143] If the extender used is water, it is also possible to use forexample organic solvents as auxiliary solvents. Suitable liquid solventsessentially include: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol and their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and water.

[0144] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates, suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and synthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; suitable emulsifiers and/or foam-formers are: for examplenonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

[0145] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, and naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0146] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyes,such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

[0147] The formulations in general contain between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0148] For controlling weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

[0149] Possible components for the mixtures are known herbicides, forexample anilides, such as diflufenican and propanil; arylcarboxylicacids, such as dichloropicolinic acid, dicamba and picloram;aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA,MCPP and triclopyr; aryloxy-phenoxy-alkanoicesters, such as, forexample, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl,haloxyfop-methyl and quizalofop-ethyl; azinones, such as, for example,chloridazon and norflurazon; carbamates, such as, for example,chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides,such as, for example, alachlor, acetochlor, butachlor, metazachlor,metolachlor, pretilachlor and propachlor; dinitroanilines, such as, forexample, oryzalin, pendimethalin and trifluralin; diphenyl ethers, suchas, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen,halosafen, lactofen and oxyfluorfen; ureas, such as, for example,chlorotoluron, diuron, fluometuron, isoproturon, linuron andmethabenzthiazuron;hydroxylamines, such as, for example, alloxydim,clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, suchas, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin;nitriles, such as, for example, bromoxynil, dichlobenil and ioxynil;oxyacetamides, such as, for example, mefenacet; sulphonylureas, such asamidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron,pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron andtribenuron-methyl; thiocarbamates, such as, for example, butylate,cycloate, diallate, EPTC, esprocarb, molinate, prosulphocarb,thiobencarb and triallate; triazines, such as atrazine, cyanazine,simazine, simetryne, terbutryne and terbutylazine; triazinones, such ashexazinone, metamitron and metribuzin; and others, such as, for example,aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

[0150] Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

[0151] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

[0152] The active compounds according to the invention can be appliedeither before or after emergence of the plants. They can also beincorporated into the soil before sowing.

[0153] The amount of active compound used can vary within a wide range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

[0154] The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1

[0155]

[0156] (Process (a))

[0157] 7.5 g (32 mmol) of4-methyl-2-methoxycarbonyl-thiophene-3-sulphonamide and 4.9 g (32 mmol)of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) are added successively toa solution of 7.9 g (30 mmol) of5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-onein 150 ml of acetonitrile. The reaction mixture is stirred at roomtemperature (about 20° C.) for about 15 hours and subsequentlyconcentrated using water pump vacuum. The residue is then taken up inmethylene chloride and washed with 1N hydrochloric acid and then withwater. The organic phase is dried over magnesium sulphate and filtered.The filtrate is concentrated using water pump vacuum and the residue isrecrystallized from isopropanol.

[0158] 9.2 g (76% of theory) of5-ethoxy-4-methyl-2-(4-methyl-2-methoxycarbonyl-thien-3-yl-sulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 169° C. are obtained.

Example 2

[0159]

[0160] (Process (b))

[0161] 2.1 g (8 mmol) of 2-ethoxycarbonyl-4-methyl-thien-3-yl-sulphonylisocyanate are added to a solution of 1.35 g (8 mmol) of4-methyl-5-propargylthio-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml ofacetonitrile. The mixture is then heated under reflux for 8 hours andsubsequently concentrated using water pump vacuum, the residue isstirred with diethyl ether and the crystalline product is isolated byfiltration with suction.

[0162] 1.4 g (40% of theory) of4-methyl-5-propargylthio-2-(2-ethoxycarbonyl-4-methyl-thien-3-yl-sulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 175° C. are obtained.

Example 3

[0163]

[0164] (Process (c))

[0165] A solution of 3.8 g (20 mmol) of4-ethoxy-5-ethylthio-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml ofacetonitrile is admixed with 6.0 g (24 mmol) of2-methyl-6-methoxy-carbonyl-benzenesulphonyl chloride, 2.6 g (40 mmol)of sodium cyanate and 1.2 g (15 mmol) of pyridine, and the reactionmixture is stirred at room temperature (about 20° C.) for 3 days. Themixture is then diluted with approximately identical volumina ofmethylene chloride and water to about three times its volume and thenmade weakly acidic (pH˜3) using 1N hydrochloric acid. The organic phaseis separated off, dried over sodium sulphate and filtered. The filtrateis concentrated and the residue is recrystallized from isopropanol.

[0166] 5.0 g (56% of theory) of4-ethoxy-5-ethylthio-2-(2-methyl-6-methoxy-carbonyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 135° C. are obtained.

Example 4

[0167]

(Process (d))

[0168] At 20° C. to a maximum of 35° C., 2.0 g (36 mmol) of potassiumhydroxide powder are added to a solution of 1.52 g (12.0 mmol) of5-methyl-1,2,4-oxadiazole-3-carboxamide in 150 ml of dioxane. After 30minutes, about 50 ml of dioxane are distilled off at 30° C. to 35° C.using water pump vacuum. The mixture is subsequently admixed a little ata time with 3.6 g (12.6 mmol) of4-methyl-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride and thereaction mixture is stirred at room temperature (about 20° C.) for about12 hours. The mixture is subsequently concentrated using water pumpvacuum and the residue is taken up in water and acidified using 2Nhydrochloric acid. The mixture is then extracted twice using 100 ml ofmethylene chloride each time. The combined organic solutions are washedwith water, dried over magnesium sulphate and filtered. The filtrate isconcentrated using water pump vacuum and the residue is recrystallizedfrom ethanol.

[0169] 2.3 g (52% of theory) ofN-(4-methyl-2-i-propoxycarbonyl-thien-3-yl-sulphonyl)-5-methyl-1,2,4-oxadiazole-3-carboxamideof melting point 142° C. are obtained.

[0170] Similar to Examples 1 to 4, and according to the generaldescription of the preparation processes according to the invention, itis also possible to prepare for example the compounds of the formula (I)listed in Table 1 below.

TABLE 1 Examples of compounds of the formula (I) Ex. Melting No. A Q R¹R² R³ point (° C.) 5 S O CH₃ CH₃

178 6 S O CH₃ CH₃

192 7 CH═CH O C₂H₅ CH₃

154 8 CH═CH O C₃H₇-i CH₃

124 9 CH═CH O CH₃ CH₃

115 10 CH═CH O C₂H₅ CH₃

 85 11 CH═CH O C₃H₇-n CH₃

 59 12 CH═CH O C₃H₇-i CH₃

(amorphous) 13 S O CH₃ CH₃

157 14 S O CH₃ CH₃

158 15 CH═CH O C₂H₅ CH₃

168 16 CH═CH O C₃H₇-i CH₃

144 17 CH═CH O C₃H₇-i CH₃

122 18 CH═CH O C₃H₇-i CH₃

167 19 CH═CH O C₃H₇-i CH₃

114 20 CH═CH O C₃H₇-n CH₃

142 21 CH═CH O C₃H₇-n CH₃

106 22 CH═CH O C₃H₇-n CH₃

105 23 CH═CH O C₃H₇-n CH₃

112 24 CH═CH O C₃H₇-n CH₃

115 25 CH═CH O C₃H₇-n CH₃

 77 26 CH═CH O C₃H₇-i CH₃

131 27 S O CH₃ CH₃

158 28 S O CH₃ CH₃

175 29 S O CH₃ CH₃

151 30 S O CH₃ CH₃

155 31 S O CH₃ CH₃

184 32 S O CH₃ CH₃

151 33 S O CH₃ CH₃

191 34 S O CH₃ CH₃

142 35 S O CH₃ CH₃

122 36 S O CH₃ CH₃

121 37 S O CH₃ CH₃

187 38 S O CH₃ CH₃

163 39 S O CH₃ CH₃

124 40 S O CH₃ CH₃

162 41 S O CH₃ CH₃

144 42 CH═CH O C₃H₇-i CH₃

125 43 CH═CH O C₃H₇-i CH₃

120 44 CH═CH O C₃H₇-i CH₃

121 45 CH═CH O C₃H₇-n CH₃

118 46 CH═CH O C₃H₇-i CH₃

130 47 CH═CH O C₃H₇-n CH₃

107 48 CH═CH O C₃H₇-n CH₃

 87 49 CH═CH O CH₂CF₃ CH₃

113 50 CH═CH O C₃H₇-n CH₃

122 51 S O CH₃ CH₃

137 52 S O CH₃ CH₃

185 53 S O CH₃ CH₃

184 54 S O C₂H₅ CH₃

161 55 S O C₂H₅ CH₃

131 56 S O C₂H₅ CH₃

158 57 S O C₂H₅ CH₃

178 58 S O C₂H₅ CH₃

133 59 S O C₂H₅ CH₃

131 60 S O C₂H₅ CH₃

159 61 S O C₂H₅ CH₃

132 62 S O C₂H₅ CH₃

150 63 S O C₂H₅ CH₃

142 64 S O C₂H₅ CH₃

108 65 S O C₂H₅ CH₃

123 66 S O C₂H₅ CH₃

135 67 S O C₂H₅ CH₃

 77 68 S O C₂H₅ CH₃

130 69 S O C₂H₅ CH₃

141 70 S O C₂H₅ CH₃

141 71 CH═CH O C₃H₇-i CF₃

 73 72 S O C₂H₅ CH₃

139 73 CH═CH O CH₃ OCF₃

181 74 CH═CH O CH₃ OCF₃

107 75 S O C₃H₇-n CH₃

114 76 S O C₃H₇-i CH₃

152 77 S O C₃H₇-i CH₃

146 78 S O C₃H₇-i CH₃

164 79 S O C₃H₇-n CH₃

167 80 S O C₃H₇-n CH₃

113 81 S O C₃H₇-i CH₃

131 82 S O C₃H₇-i CH₃

173 83 S O C₃H₇-i CH₃

 87 84 S O C₃H₇-i CH₃

125 85 S O C₃H₇-i CH₃

127 86 S O C₃H₇-i CH₃

126 87 S O C₃H₇-i CH₃

136 88 S O C₂H₅ CH₃

106 89 S O C₃H₇-n CH₃

117 90 S O C₃H₇-n CH₃

 90 91 S O C₃H₇-n CH₃

134 92 S O C₃H₇-n CH₃

141 93 S O C₃H₇-n CH₃

142 94 S O C₃H₇-n CH₃

 90 95 S O C₃H₇-n CH₃

119 96 S O C₃H₇-i CH₃

159 97 S O C₃H₇-i CH₃

130 98 S O C₃H₇-i CH₃

145 99 S O C₃H₇-n CH₃

109 100 S O C₃H₇-n CH₃

 95 101 S O C₃H₇-n CH₃

 84 102 S O C₃H₇-n CH₃

 89 103 S O C₃H₇-n CH₃

135 104 S O C₂H₅ CH₃

155 105 S O C₂H₅ CH₃

116 106 S O C₂H₅ CH₃

136 107 S O C₃H₇-i CH₃

135 108 S O C₃H₇-i CH₃

 98 109 S O C₃H₇-i CH₃

120 110 S O C₃H₇-i CH₃

140 111 S O C₃H₇-i CH₃

137 112 S O C₃H₇-i CH₃

145 113 S O C₃H₇-i CH₃

124 114 S O C₃H₇-n CH₃

108 115 S O C₃H₇-n CH₃

138 116 S O C₃H₇-n CH₃

 93 117 S O C₃H₇-n CH₃

130 118 S O C₃H₇-n CH₃

128 119 S O CH₃ CH₃

248 (Na salt) 120 CH═CH O CH₃ Cl

 78 121 CH═CH O CH₃ CH₃

120 122 CH═CH O CH₃ Cl

 68 123 CH═CH O CH₃ CH₃

 54 124 CH═CH O CH₃ Cl

147 125 CH═CH O CH₃ CH₃

118 126 CH═CH O CH₃ Cl

 63 127 CH═CH O CH₃ Cl

167 128 CH═CH O C₂H₅ Cl

128 129 CH═CH O CH₃ Cl

 95 130 CH═CH O CH₃ Cl

153 131 CH═CH O C₂H₅ Cl

145 132 CH═CH O C₃H₇-n Cl

 98 133 CH═CH O C₃H₇-n Cl

 89 134 CH═CH O C₃H₇-n Cl

110 135 CH═CH O CH₃ OCH₃

175 136 CH═CH O CH₃ OCH₃

190 137 CH═CH O C₃H₇-i Cl

 89 138 CH═CH O

CH₃

146 139 CH═CH O

CH₃

158 140 CH═CH O CH₃ CH₃

150 141 CH═CH O CH₃ CH₃

142 142 CH═CH O CH₃ CH₃

145 143 CH═CH O CH₃ CH₃

148 144 CH═CH O CH₃ CH₃

155 (Na salt) 145 CH═CH O CH₃ CH₃

185 (Na salt) 146 CH═CH O CH₃ CH₃

163 147 CH═CH O CH₃ CH₃

122 148 CH═CH O CH₃ CH₃

137 149 CH═CH O CH₃ CH₃

156 150 CH═CH O CH₃ CH₃

122 151 CH═CH O CH₃ CH₃

166 152 CH═CH O CH₃ CH₃

125 153 CH═CH O CH₃ CH₃

137 154 CH═CH O CH₃ CH₃

179 (Na salt) 155 CH═CH O CH₃ CH₃

153 156 CH═CH O CH₃ CH₃

172 157 CH═CH O CH₃ CH₃

124 158 CH═CH O CH₃ CH₃

157 159 CH═CH O CH₃ CH₃

156 160 CH═CH O CH₃ CH₃

138 161 CH═CH O CH₃ CH₃

137 162 CH═CH O CH₃ CH₃

160 163 CH═CH O CH₃ CH₃

139 164 CH═CH O CH₃ CH₃

174 165 CH═CH O CH₃ CH₃

119 166 CH═CH O CH₃ CH₃

158 167 CH═CH O CH₃ CH₃

148 168 CH═CH O CH₃ CH₃

128 169 CH═CH O CH₃ CH₃

145 170 CH═CH O CH₃ CH₃

161 171 CH═CH O CH₃ CH₃

129 172 CH═CH O CH₃ CH₃

136 173 CH═CH O CH₃ CH₃

155 174 CH═CH O CH₃ CH₃

129 175 CH═CH O CH₃ CH₃

150 176 CH═CH O CH₃ CH₃

148 177 CH═CH O CH₃ CH₃

149 178 CH═CH O CH₃ CH₃

 99 179 CH═CH O CH₃ CH₃

115 180 CH═CH O CH₃ CH₃

114 181 CH═CH O CH₃ CH₃

125 182 CH═cH O CH₃ CH₃

124 183 CH═CH O CH₃ CH₃

105 184 CH═CH O CH₃ CH₃

131 185 CH═CH O CH₃ CH₃

149 186 S O C₃H₇-n CH₃

187 CH═CH O CH₃ NO₂

180

[0171] The compound listed as Example 119 in Table 1 can be prepared forexample as follows:

[0172] (Salt Formation)

[0173] A mixture of 2.0 g (5 mmol) of5-ethoxy-4-methyl-2-(4methyl-2-methoxy-carbonyl-thien-3-yl-sulfonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneand 75 ml of acetonitrile is admixed with 0.17 g (5.5 mmol) of sodiumhydride (80% strength), and the mixture is stirred at room temperature(about 20° C.) for about 60 minutes. The crystalline product is thenisolated by filtration with suction

[0174] 2.0 g (94% of theory) of the sodium salt of5-ethoxy-4-methyl-2-(4-methyl-2-methoxycarbonyl-thien-3-yl-sulfonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained as a colourless crystalline product of melting point 248°C.

[0175] Starting Materials of the Formula (II):

Example (II-1)

[0176]

[0177] 12.0 g (42.6 mmol) of4-methyl-2-i-propoxycarbonyl-thiophene-3-sulfonyl chloride are dissolvedin 100 ml of methylene chloride and admixed with 8.2 g (85.4 mmol) ofammonium carbonate. The mixture is stirred at room temperature (about20° C.) for about 24 hours. The undissolved salt is filtered off bysuction, the filtrate is concentrated using water pump vacuum, theresidue is digested with diethyl ether and the crystalline product isisolated by filtration with suction.

[0178] 9.1 g (91% of theory) of4-methyl-2-i-propoxycarbonyl-thiophene-3-sulphonamide are obtained as alight-yellow solid of melting point 76° C.

[0179] Similarly, it is possible to prepare for example the followingcompounds of the formula (II):

[0180] 4-methyl-2-methoxycarbonyl-thiophene-3-sulphonamide (mp.: 54°C.),

[0181] 4-methyl-2-ethoxycarbonyl-thiophene-3-sulphonamide (mp.: 65° C.),

[0182] 4-methyl-2-n-propoxycarbonyl-thiophene-3-sulphonamide (mp.: 90°C.),

[0183] 4-methyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0184] 4-ethyl-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0185] 4-ethyl-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0186] 4-ethyl-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0187] 4-ethyl-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0188] 4-ethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0189] 4-fluoro-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0190] 4-fluoro-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0191] 4-fluoro-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0192] 4-fluoro-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0193] 4-fluoro-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0194] 4-chloro-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0195] 4-chloro-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0196] 4-chloro-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0197] 4-chloro-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0198] 4-chloro-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0199] 4-bromo-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0200] 4-bromo-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0201] 4-bromo-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0202] 4-bromo-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0203] 4-bromo-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0204] 4-methoxy-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0205] 4-methoxy-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0206] 4-methoxy-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0207] 4-methoxy-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0208] 4-methoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0209] 4-methylthio-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0210] 4-methylthio-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0211] 4-methylthio-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0212] 4-methylthio-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0213]4-methylthio-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0214] 4-trifluoromethyl-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0215] 4-trifluoromethyl-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0216] 4-trifluoromethyl-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0217] 4-trifluoromethyl-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0218]4-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0219] 4-difluoromethoxy-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0220] 4-difluoromethoxy-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0221] 4-difluoromethoxy-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0222] 4-difluoromethoxy-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0223]4-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide,

[0224] 4-trifluoromethoxy-2-methoxycarbonyl-thiophene-3-sulphonamide,

[0225] 4-trifluoromethoxy-2-ethoxycarbonyl-thiophene-3-sulphonamide,

[0226] 4-trifluoromethoxy-2-n-propoxycarbonyl-thiophene-3-sulphonamide,

[0227] 4-trifluoromethoxy-2-i-propoxycarbonyl-thiophene-3-sulphonamide,

[0228]4-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonamide.

[0229] 6-methyl-2-methoxycarbonyl-benzenesulphonamide (mp.: 118° C.),

[0230] 6-methyl-2-ethoxycarbonyl-benzenesulphonamide (mp.: 277° C.),

[0231] 6-methyl-2-n-propoxycarbonyl-benzenesulphonamide,

[0232] 6-methyl-2-i-propoxycarbonyl-benzenesulphonamide (mp.:122° C.),

[0233] 6-methyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0234] 6-ethyl-2-methoxycarbonyl-benzenesulphonamide,

[0235] 6-ethyl-2-ethoxycarbonyl-benzenesulphonamide,

[0236] 6-ethyl-2-n-propoxycarbonyl-benzenesulphonamide,

[0237] 6-ethyl-2-i-propoxycarbonyl-benzenesulphonamide,

[0238] 6-ethyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0239] 6-fluoro-2-methoxycarbonyl-benzenesulphonamide,

[0240] 6-fluoro-2-ethoxycarbonyl-benzenesulphonamide,

[0241] 6-fluoro-2-n-propoxycarbonyl-benzenesulphonamide,

[0242] 6-fluoro-2-i-propoxycarbonyl-benzenesulphonamide,

[0243] 6-fluoro-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0244] 6-chloro-2-methoxycarbonyl-benzenesulphonamide,

[0245] 6-chloro-2-ethoxycarbonyl-benzenesulphonamide,

[0246] 6-chloro-2-n-propoxycarbonyl-benzenesulphonamide,

[0247] 6-chloro-2-i-propoxycarbonyl-benzenesulphonamide,

[0248] 6-chloro-2-(oxetan-2-yl-oxycarbonyl)-benzene-sulphonamide,

[0249] 6-bromo-2-methoxycarbonyl-benzenesulphonarnide,

[0250] 6-bromo-2-ethoxycarbonyl-benzenesulphonarnide,

[0251] 6-bromo-2-n-propoxycarbonyl-benzenesulphonamide,

[0252] 6-bromo-2-i-propoxycarbonyl-benzenesulphonamide,

[0253] 6-bromo-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0254] 6-methoxy-2-methoxycarbonyl-benzenesulphonamide,

[0255] 6-methoxy-2-ethoxycarbonyl-benzenesulphonamide,

[0256] 6-methoxy-2-n-propoxycarbonyl-benzenesulphonamide,

[0257] 6-methoxy-2-i-propoxycarbonyl-benzenesulphonarnide,

[0258] 6-methoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0259] 6-methylthio-2-methoxycarbonyl-benzenesulphonamide,

[0260] 6-methylthio-2-ethoxycarbonyl-benzenesulphonamide,

[0261] 6-methylthio-2-n-propoxycarbonyl-benzenesulphonamide,

[0262] 6-methylthio-2-i-propoxycarbonyl-benzenesulphonamide,

[0263] 6-methylthio-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0264] 6-trifluoromethyl-2-methoxycarbonyl-benzenesulphonamide,

[0265] 6-trifluoromethyl-2-ethoxycarbonyl-benzenesulphonamide,

[0266] 6-trifluoromethyl-2-n-propoxycarbonyl-benzenesulphonamide,

[0267] 6-trifluoromethyl-2-i-propoxycarbonyl-benzenesulphonamide,

[0268]6-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0269] 6-difluoromethoxy-2-methoxycarbonyl-benzenesulphonamide,

[0270] 6-difluoromethoxy-2-ethoxycarbonyl-benzenesulphonamide,

[0271] 6-difluoromethoxy-2-n-propoxycarbonyl-benzenesulphonamide,

[0272] 6-difluoromethoxy-2-i-propoxycarbonyl-benzenesulphonamide,

[0273]6-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide,

[0274] 6-trifluoromethoxy-2-methoxycarbonyl-benzenesulphonamide,

[0275] 6-trifluoromethoxy-2-ethoxycarbonyl-benzenesulphonamide,

[0276] 6-trifluoromethoxy-2-n-propoxycarbonyl-benzenesulphonamide,

[0277] 6-trifluoromethoxy-2-i-propoxycarbonyl-benzenesulphonamide,

[0278]6-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonamide.

[0279] Starting Materials of the Formula (IV):

Example (IV-1)

[0280]

[0281] A mixture of 25 g (95 mmol) of4-methyl-2-methoxycarbonyl-thiophene-3-sulphonamide, 9.4 g (95 mmol) ofn-butyl isocyanate and 100 ml of chlorobenzene is heated to boilingpoint, and at reflux temperature, phosgene is introduced for 4 hours.The mixture is subsequently concentrated using water pump vacuum and theresidue is purified by distillation under reduced pressure (2 mbar).

[0282] 11 g (40% of theory) of4-methyl-2-methoxycarbonyl-thiophen-3-yl-sulfonyl isocyanate of aboiling range of 140° C.-145° C. (at 2 mbar), which solidify to givecolourless crystals, are obtained.

[0283] Similarly, it is possible to prepare for example the followingcompounds of the formula (II):

[0284] 4-methyl-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0285] 4-methyl-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0286] 4-methyl-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0287] 4-methyl-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0288] 4-ethyl-2-methoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0289] 4-ethyl-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0290] 4-ethyl-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0291] 4-ethyl-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0292] 4-ethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0293] 4-fluoro-2-methoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0294] 4-fluoro-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0295] 4-fluoro-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0296] 4-fluoro-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0297] 4-fluoro-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0298] 4-chloro-2-methoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0299] 4-chloro-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0300] 4-chloro-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0301] 4-chloro-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0302] 4-chloro-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0303] 4-bromo-2-methoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0304] 4-bromo-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0305] 4-bromo-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0306] 4-bromo-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0307] 4-bromo-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0308] 4-methoxy-2-methoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0309] 4-methoxy-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0310] 4-methoxy-2-n-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0311] 4-methoxy-2-i-propoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0312] 4-methoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0313] 4-methylthio-2-methoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0314] 4-methylthio-2-ethoxycarbonyl-thiophen-3-yl-sulphonyl isocyanate,

[0315] 4-methylthio-2-n-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0316] 4-methylthio-2-i-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0317] 4-methylthio-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0318] 4-trifluoromethyl-2-methoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0319] 4-trifluoromethyl-2-ethoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0320] 4-trifluoromethyl-2-n-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0321] 4-trifluoromethyl-2-i-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0322]4-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0323] 4-difluoromethoxy-2-methoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0324] 4-difluoromethoxy-2-ethoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0325] 4-difluoromethoxy-2-n-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0326] 4-difluoromethoxy-2-i-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0327]4-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0328] 4-trifluoromethoxy-2-methoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0329] 4-trifluoromethoxy-2-ethoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0330] 4-trifluoromethoxy-2-n-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0331] 4-trifluoromethoxy-2-i-propoxycarbonyl-thiophen-3-yl-sulphonylisocyanate,

[0332]4-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophen-3-yl-sulphonylisocyanate,

[0333] 6-methyl-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0334] 6-methyl-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0335] 6-methyl-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0336] 6-methyl-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0337] 6-methyl-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0338] 6-ethyl-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0339] 6-ethyl-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0340] 6-ethyl-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0341] 6-ethyl-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0342] 6-ethyl-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0343] 6-fluoro-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0344] 6-fluoro-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0345] 6-fluoro-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0346] 6-fluoro-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0347] 6-fluoro-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0348] 6-chloro-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0349] 6-chloro-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0350] 6-chloro-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0351] 6-chloro-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0352] 6-chloro-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0353] 6-bromo-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0354] 6-bromo-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0355] 6-bromo-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0356] 6-bromo-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0357] 6-bromo-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0358] 6-methoxy-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0359] 6-methoxy-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0360] 6-methoxy-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0361] 6-methoxy-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0362] 6-methoxy-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonyl isocyanate,

[0363] 6-methylthio-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0364] 6-methylthio-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0365] 6-methylthio-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0366] 6-methylthio-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0367] 6-methylthio-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonylisocyanate,

[0368] 6-trifluoromethyl-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0369] 6-trifluoromethyl-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0370] 6-trifluoromethyl-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0371] 6-trifluoromethyl-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0372] 6-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonylisocyanate,

[0373] 6-difluoromethoxy-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0374] 6-difluoromethoxy-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0375] 6-difluoromethoxy-2-n-propoxycarbonyl-phenylsulphonyl isocyanate,

[0376] 6-difluoromethoxy-2-i-propoxycarbonyl-phenylsulphonyl isocyanate,

[0377] 6-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonylisocyanate,

[0378] 6-trifluoromethoxy-2-methoxycarbonyl-phenylsulphonyl isocyanate,

[0379] 6-trifluoromethoxy-2-ethoxycarbonyl-phenylsulphonyl isocyanate,

[0380] 6-trifluoromethoxy-2-n-propoxycarbonyl-phenylsulphonylisocyanate,

[0381] 6-trifluoromethoxy-2-i-propoxycarbonyl-phenylsulphonylisocyanate,

[0382] 6-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-phenylsulphonylisocyanate.

[0383] Starting Materials of the Formula (VI):

Example (VI-1)

[0384]

[0385] A solution of 21.2 g (90 mmol) of i-propyl3-amino-4-methyl-thiophene-2-carboxylate hydrochloride in 60 ml of conc.hydrochloric acid is cooled to about −10° C., and a solution of 6.9 g(100 mmol) of sodium nitrite in 13 ml of water is then added dropwisewith stirring to this mixture at −10° C. to −5° C. The reaction mixtureis stirred at −5° C. to 0° C. for about 60 minutes. The resultingdiazonium salt solution is added dropwise at about 15° C. to a solutionof 50 g of sulphur dioxide in 110 ml of acetic acid containing 10 ml ofa saturated aqueous solution of copper(II) chloride. The mixture isstirred at room temperature (about 20° C.) for 12 hours and then dilutedwith about 500 ml of methylene chloride, washed twice with ice-water,dried over magnesium sulphate and filtered. The filtrate is concentratedusing water pump vacuum, the residue is digested with petroleum etherand the resulting crystalline product is isolated by filtration withsuction.

[0386] 17.0 g of (67% of theory) of4-methyl-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride are obtainedas a yellow solid of melting point 58° C. Similarly, it is possible toprepare for example the following compounds of the formula (VI):

[0387] 4-methyl-2-methoxycarbonyl-thiophene-3-sulphonyl chloride (mp.:56° C.),

[0388] 4-methyl-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride (mp.:47° C.),

[0389] 4-methyl-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride (mp.:42° C.),

[0390] 4-methyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0391] 4-ethyl-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0392] 4-ethyl-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0393] 4-ethyl-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0394] 4-ethyl-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0395] 4-ethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0396] 4-fluoro-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0397] 4-fluoro-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0398] 4-fluoro-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0399] 4-fluoro-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0400] 4-fluoro-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0401] 4-chloro-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0402] 4-chloro-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0403] 4-chloro-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0404] 4-chloro-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0405] 4-chloro-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0406] 4-bromo-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0407] 4-bromo-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0408] 4-bromo-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0409] 4-bromo-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0410] 4-bromo-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0411] 4-methoxy-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0412] 4-methoxy-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0413] 4-methoxy-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0414] 4-methoxy-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0415] 4-methoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0416] 4-methylthio-2-methoxycarbonyl-thiophene-3-sulphonyl chloride,

[0417] 4-methylthio-2-ethoxycarbonyl-thiophene-3-sulphonyl chloride,

[0418] 4-methylthio-2-n-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0419] 4-methylthio-2-i-propoxycarbonyl-thiophene-3-sulphonyl chloride,

[0420] 4-methylthio-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0421] 4-trifluoromethyl-2-methoxycarbonyl-thiophene-3-sulphonylchloride,

[0422] 4-trifluoromethyl-2-ethoxycarbonyl-thiophene-3-sulphonylchloride,

[0423] 4-trifluoromethyl-2-n-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0424] 4-trifluoromethyl-2-i-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0425]4-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0426] 4-difluoromethoxy-2-methoxycarbonyl-thiophene-3-sulphonylchloride,

[0427] 4-difluoromethoxy-2-ethoxycarbonyl-thiophene-3-sulphonylchloride,

[0428] 4-difluoromethoxy-2-n-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0429] 4-difluoromethoxy-2-i-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0430]4-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride,

[0431] 4-trifluoromethoxy-2-methoxycarbonyl-thiophene-3-sulphonylchloride,

[0432] 4-trifluoromethoxy-2-ethoxycarbonyl-thiophene-3-sulphonylchloride,

[0433] 4-trifluoromethoxy-2-n-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0434] 4-trifluoromethoxy-2-i-propoxycarbonyl-thiophene-3-sulphonylchloride,

[0435]4-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-thiophene-3-sulphonylchloride.

[0436] 6-methyl-2-methoxycarbonyl-benzenesulphonyl chloride (mp.: 109°C.),

[0437] 6-methyl-2-ethoxycarbonyl-benzenesulphonyl chloride (mp.: 82°C.),

[0438] 6-methyl-2-n-propoxycarbonyl-benzenesulphonyl chloride (mp.: 52°C.),

[0439] 6-methyl-2-i-propoxycarbonyl-benzenesulphonyl chloride (mp.: 51°C.),

[0440] 6-methyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonyl chloride,

[0441] 6-ethyl-2-methoxycarbonyl-benzenesulphonyl chloride,

[0442] 6-ethyl-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0443] 6-ethyl-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0444] 6-ethyl-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0445] 6-ethyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonyl chloride,

[0446] 6-fluoro-2-methoxycarbonyl-benzenesulphonyl chloride,

[0447] 6-fluoro-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0448] 6-fluoro-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0449] 6-fluoro-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0450] 6-fluoro-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonyl chloride,

[0451] 6-chloro-2-methoxycarbonyl-benzenesulphonyl chloride,

[0452] 6-chloro-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0453] 6-chloro-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0454] 6-chloro-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0455] 6-chloro-2-(oxetan-2-yl-oxycarbonyl)-benzene-sulphonyl chloride,

[0456] 6-bromo-2-methoxycarbonyl-benzenesulphonyl chloride,

[0457] 6-bromo-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0458] 6-bromo-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0459] 6-bromo-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0460] 6-bromo-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonyl chloride,

[0461] 6-methoxy-2-methoxycarbonyl-benzenesulphonyl chloride,

[0462] 6-methoxy-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0463] 6-methoxy-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0464] 6-methoxy-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0465] 6-methoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonyl chloride,

[0466] 6-methylthio-2-methoxycarbonyl-benzenesulphonyl chloride,

[0467] 6-methylthio-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0468] 6-methylthio-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0469] 6-methylthio-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0470] 6-methylthio-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonylchloride,

[0471] 6-trifluoromethyl-2-methoxycarbonyl-benzenesulphonyl chloride,

[0472] 6-trifluoromethyl-2-ethoxycarbonyl-benzenesulphonyl chloride(amorphous),

[0473] 6-trifluoromethyl-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0474] 6-trifluoromethyl-2-i-propoxycarbonyl-benzenesulphonyl chloride(mp.: 64° C.),

[0475] 6-trifluoromethyl-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonylchloride,

[0476] 6-difluoromethoxy-2-methoxycarbonyl-benzenesulphonyl chloride,

[0477] 6-difluoromethoxy-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0478] 6-difluoromethoxy-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0479] 6-difluoromethoxy-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0480] 6-difluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonylchloride,

[0481] 6-trifluoromethoxy-2-methoxycarbonyl-benzenesulphonyl chloride,

[0482] 6-trifluoromethoxy-2-ethoxycarbonyl-benzenesulphonyl chloride,

[0483] 6-trifluoromethoxy-2-n-propoxycarbonyl-benzenesulphonyl chloride,

[0484] 6-trifluoromethoxy-2-i-propoxycarbonyl-benzenesulphonyl chloride,

[0485] 6-trifluoromethoxy-2-(oxetan-2-yl-oxycarbonyl)-benzenesulphonylchloride.

[0486] Starting Materials of the Formula (X):

Example (X-1)

[0487]

[0488] With shaking, a mixture of 192 g (1.43 mol) of i-propylmercaptoacetate and 183 g (1.43 mol) of i-propyl methacrylate is admixedwith 5 drops of piperidine. The mixture is heated to 50° C., admixedwith a further 20 drops of piperidine and stirred at a bath temperatureof 100° C. for 12 hours. The mixture is subsequently distilled underreduced pressure.

[0489] 288 g (77% of theory) of i-propyl2-methyl-3-(i-propoxycarbonylmethylthio)-propionate are obtained as acolourless oil of a boiling range of 135° C. to 140° C. at 2 mbar.

[0490] Similarly, it is possible to prepare for example the followingcompounds:

[0491] methyl 2-methyl-3-(methoxycarbonylmethylthio)-propionate,

[0492] ethyl 2-methyl-3-(ethoxycarbonylmethylthio)-propionate (bp.: 105°C. to 112° C. at 1 mbar),

[0493] n-propyl 2-methyl-3-(n-propoxycarbonylmethylthio)-propionate(bp.: 145° C. to 147° C. at 3 mbar),

[0494] methyl 2-methyl-3-(ethoxycarbonylmethylthio)-propionate (bp.:150° C. to 152° C. at 0.1 mbar),

[0495] methyl 2-methyl-3-(n-propoxycarbonylmethylthio)-propionate (bp.:158° C. to 160° C. at 0.1 mbar),

[0496] methyl 2-methyl-3 -(i-propoxycarbonylmethylthio)-propionate (bp.:162° C. to 165° C. at 0.1 mbar),

[0497] methyl 2-ethyl-3-(methoxycarbonylmethylthio)-propionate,

[0498] ethyl 2-ethyl-3-(ethoxycarbonylmethylthio)-propionate,

[0499] n-propyl 2-ethyl-3-(n-propoxycarbonylmethylthio)-propionate,

[0500] i-propyl 2-ethyl-3-(i-propoxycarbonylmethylthio)-propionate,

[0501] methyl 2-ethyl-3-(ethoxycarbonylmethylthio)-propionate,

[0502] methyl 2-ethyl-3-(n-propoxycarbonylmethylthio)-propionate,

[0503] methyl 2-ethyl-3-(i-propoxycarbonylmethylthio)-propionate,

[0504] methyl2-trifluoromethyl-3-(methoxycarbonylmethylthio)-propionate,

[0505] ethyl 2-trifluoromethyl-3-(ethoxycarbonylmethylthio)-propionate,

[0506] n-propyl2-trifluoromethyl-3-(n-propoxycarbonylmethylthio)-propionate,

[0507] i-propyl2-trifluoromethyl-3-(i-propoxycarbonylmethylthio)-propionate,

[0508] methyl 2-trifluoromethyl-3-(ethoxycarbonylmethylthio)-propionate,

[0509] methyl2-trifluoromethyl-3-(n-propoxycarbonylmethylthio)-propionate,

[0510] methyl 2-trifluoromethyl-3-(i-propoxycarbonylmethylthio)-propionate,

[0511] methyl 2-chloro-3-(methoxycarbonylmethylthio)-propionate,

[0512] ethyl 2-chloro-3-(ethoxycarbonylmethylthio)-propionate,

[0513] n-propyl 2-chloro-3-(n-propoxycarbonylmethylthio)-propionate,

[0514] i-propyl 2-chloro-3-(i-propoxycarbonylmethylthio)-propionate,

[0515] methyl 2-chloro-3-(ethoxycarbonylmethylthio)-propionate,

[0516] methyl 2-chloro-3-(n-propoxycarbonylmethylthio)-propionate,

[0517] methyl 2-chloro-3-(i-propoxycarbonylmethylthio)-propionate.

[0518] Step 2

[0519] At room temperature (about 20° C.), 480 g (1.83 mol) of i-propyl2-methyl-3-(i-propoxycarbonylmethylthio)-propionate are added dropwiseto a suspension of 246 g (3.0 mol) of sodium i-propoxide in 1 litre oftoluene, and the mixture is then stirred at about 90° C. for about 12hours. The mixture is subsequently poured into ice-cold 2N hydrochloricacid. This mixture is then extracted three times with diethyl ether andthe combined extracts are washed twice with water. The organic phase isdried over magnesium sulphate and filtered. The filtrate is concentratedusing water pump vacuum and the residue is distilled under reducedpressure.

[0520] 254 g (69% of theory) of i-propyl4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate are obtained as alight-yellow oil of boiling point 11 9° C. to 120° C. at I mbar.

[0521] Similarly, it is possible to prepare for example the followingcompounds:

[0522] methyl 4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0523] ethyl 4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate (bp.: 112°C. at 4 mbar),

[0524] n-propyl 4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate (bp.:127° C. to 128° C. at 1 mbar),

[0525] methyl 4-ethyl-3 -oxo-tetrahydrothiophene-2-carboxylate,

[0526] ethyl 4-ethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0527] n-propyl 4-ethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0528] i-propyl 4-ethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0529] methyl 4-trifluoromethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0530] ethyl 4-trifluoromethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0531] n-propyl4-trifluoromethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0532] i-propyl4-trifluoromethyl-3-oxo-tetrahydrothiophene-2-carboxylate,

[0533] methyl 4-chloro-3-oxo-tetrahydrothiophene-2-carboxylate,

[0534] ethyl 4-chloro-3-oxo-tetrahydrothiophene-2-carboxylate,

[0535] n-propyl 4-chloro-3-oxo-tetrahydrothiophene-2-carboxylate,

[0536] i-propyl 4-chloro-3-oxo-tetrahydrothiophene-2-carboxylate.

[0537] Step 3

[0538] A mixture of 505 g (2.5 mol) of i-propyl4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate, 497 g (7.2 mol) ofhydroxylamine hydrochloride, 753 g (3.8 mol) of barium carbonate and 2.5litres of isopropanol is heated under reflux for about 12 hours. Themixture is subsequently filtered off with suction, the filter cake iswashed with hot isopropanol and the filtrate is concentrated using waterpump vacuum. The residue is taken up in 2 litres of diethyl ether,washed twice with water, dried over magnesium sulphate and filtered. Thesolvent is carefully distilled off from the filtrate using water pumpvacuum.

[0539] 445 g (82% of theory) of 1-propyl4-methyl-3-hydroximino-tetrahydrothiophene-2-carboxylate are obtained asa light-yellow oily crude product which is employed without any furtherpurification for the next step.

[0540] Similarly, it is possible to prepare for example the followingcompounds:

[0541] methyl 4-methyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0542] ethyl 4-methyl-3-hydroximino-tetrahydrothiophene-2-carboxylate(colourless oil),

[0543] n-propyl 4-methyl-3-hydroximino-tetrahydrothiophene-2-carboxylate(light-yellow oil),

[0544] methyl 4-ethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0545] ethyl 4-ethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0546] n-propyl 4-ethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0547] i-propyl 4-ethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0548] methyl4-trifluoromethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0549] ethyl4-trifluoromethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0550] n-propyl4-trifluoromethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0551] i-propyl4-trifluoromethyl-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0552] methyl 4-chloro-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0553] ethyl 4-chloro-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0554] n-propyl4-chloro-3-hydroximino-tetrahydrothiophene-2-carboxylate,

[0555] i-propyl4-chloro-3-hydroximino-tetrahydrothiophene-2-carboxylate.

[0556] Step 4

[0557] 334 g (1.54 mol) of i-propyl4-methyl-3-hydroximino-tetrahydrothiophene-2-carboxylate are dissolvedin 5 litres of methyl tert-butyl ether and cooled using an ice bath.Hydrogen chloride is then—after the ice bath had been removed—introducedwith stirring for two hours. The mixture is subsequently concentratedusing water pump vacuum and the amorphous residue is crystallized fromacetone.

[0558] 358 g (99% of theory) of i-propyl3-amino-4-methyl-thiophene-2-carboxylate hydrochloride are obtained as abeige-coloured solid of melting point 153° C.

[0559] Similarly, it is possible to prepare for example the followingcompounds:

[0560] ethyl 3-amino-4-methyl-thiophene-2-carboxylate hydrochloride(mp.: 133° C.),

[0561] n-propyl 3-amino-4-methyl-thiophene-2-carboxylate hydrochloride(mp.: 152° C.),

[0562] ethyl 3-amino-4-ethyl-thiophene-2-carboxylate hydrochloride,

[0563] n-propyl 3-amino-4-ethyl-thiophene-2-carboxylate hydrochloride,

[0564] i-propyl 3-amino-4-ethyl-thiophene-2-carboxylate hydrochloride,

[0565] ethyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylatehydrochloride,

[0566] n-propyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylatehydrochloride,

[0567] i-propyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylatehydrochloride,

[0568] ethyl 3-amino-4-chloro-thiophene-2-carboxylate hydrochloride,

[0569] n-propyl 3-amino-4-chloro-thiophene-2-carboxylate hydrochloride,

[0570] i-propyl 3-amino-4-chloro-thiophene-2-carboxylate hydrochloride.

[0571] Step 5

[0572] 11.75 g (50 mmol) of i-propyl3-amino-4-methyl-thiophene-2-carboxylate hydrochloride are dissolved in100 ml of water. 150 ml of methylene chloride are added to thissolution, and sodium bicarbonate is then added a little at a time untila pH of 7 has been exceeded. The mixture is stirred for 8 hours and theorganic phase is separated off, washed with water, dried with magnesiumsulphate and filtered. The filtrate is concentrated using water pumpvacuum and the amorphous residue is crystallized from petroleum ether.

[0573] 7.2 g (73% of theory) of i-propyl3-amino-4-methyl-thiophene-2-carboxylate are obtained as abeige-coloured solid of melting point 40° C.

[0574] Similarly, it is possible to prepare for example the followingcompounds:

[0575] ethyl 3-amino-4-methyl-thiophene-2-carboxylate (mp.: 133° C.),

[0576] n-propyl 3-amino-4-methyl-thiophene-2-carboxylate (amorphous),

[0577] ethyl 3-amino-4-ethyl-thiophene-2-carboxylate,

[0578] n-propyl 3-amino-4-ethyl-thiophene-2-carboxylate,

[0579] i-propyl 3-amino-4-ethyl-thiophene-2-carboxylate,

[0580] ethyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylate,

[0581] n-propyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylate,

[0582] i-propyl 3-amino-4-trifluoromethyl-thiophene-2-carboxylate,

[0583] ethyl 3-amino-4-chloro-thiophene-2-carboxylate,

[0584] n-propyl 3-amino-4-chloro-thiophene-2-carboxylate,

[0585] i-propyl 3-amino-4-chloro-thiophene-2-carboxylate.

[0586] Use Examples:

Example A

[0587] Pre-emergence test

[0588] Solvent: 5 parts by weight of acetone

[0589] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0590] To produce a suitable preparation of the active compound, 1 partby weight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0591] Seeds of the test plants are sown in normal soil. After about 24hours, the soil is watered with the preparation of active compound.Advantageously, the amount of water per unit area is kept constant. Theactive compound concentration in the preparation is not important, onlythe active compound appliation rate per unit area matters.

[0592] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0593] The figures denote:

[0594] 0% no action (like untreated control)

[0595] 100%=total destruction

[0596] In this test, very strong activity against weeds is shown, forexample, by the compounds of Preparation Examples 1, 3, 5, 6, 7, 8, 9,10, 12, 13, 16, 17, 18, 19, 20, 21, 22, 23, 28, 30, 31, 32, 33, 34, 35,37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 51, 53, 54, 55, 56, 57,58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 70, 72, 76, 77, 80, 81, 82, 84,85, 86, 89, 93, 108, 121, 129, 130, 131, 134, 135, 136, 140, 141, 142,143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156,157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167 and 172, combinedwith predominantly good tolerance by crop plants such as, for example,maize and soya beans.

[0597] “ai.”=active compound (“active ingredient”) TABLE A Pre-emergencetest/Greenhouse Active compound of Application Preparation rate SoyaExample (g of ai./ha) Maize beans Lolium Poa Sorghum Ambrosia MatricariaSolanum 5 30 0 20 95 95 90 95 95 95 1 30 10 — 95 95 90 95 95 95 6 125 0— 95 95 95 95 95 95 7 60 0 0 95 — 95 95 95 — 8 60 30 0 95 90 80 90 95 959 125 0 — 80 80 60 95 90 95 10 250 0 20 80 90 70 95 95 95 12 125 0 0 8080 60 95 95 95 13 125 30 — 90 80 70 95 95 90 16 30 — 0 95 95 90 95 95 9517 30 — 0 80 95 60 95 95 95 18 60 10 0 80 95 90 95 95 95 19 60 0 0 95 95— 95 95 90 20 125 10 0 95 95 90 95 95 95 21 125 0 0 95 95 95 95 95 95 22125 20 10 95 95 80 95 95 95 23 125 0 0 — 80 60 90 95 90 28 60 0 — 95 9595 95 95 95 30 30 0 — 95 95 80 95 95 95 31 15 10 — 95 95 80 95 95 95 3260 20 20 95 95 60 95 95 95 33 125 10 — — 90 80 90 95 95 34 60 10 0 60 7080 90 95 90 35 60 0 — 95 95 95 95 100 95 37 60 10 10 90 70 — 80 95 90 3860 0 — 95 70 60 95 95 95 39 60 0 20 95 90 — 95 70 90 40 60 10 30 90 95 —95 95 95 41 60 0 — 60 80 60 95 95 90 42 60 10 10 95 95 — 95 95 95 43 60— 10 95 95 80 95 95 95 44 8 30 0 95 95 95 95 95 95 45 125 10 20 90 95 —95 90 95 46 8 0 — 80 95 80 95 95 95 47 125 10 10 90 90 60 95 95 95 48125 30 20 95 95 — 95 100 95 51 125 0 30 80 80 80 95 95 95 53 125 0 — 9595 — 95 95 95 54 30 0 — 95 95 80 95 95 95 55 125 10 — 100 90 60 100 100100 56 125 — 0 60 80 — — 100 95 57 60 0 — 95 95 95 — 95 95 58 125 20 —80 95 — — 100 95 59 125 0 — 100 70 — 95 100 95 61 125 0 — 95 95 80 10095 95 62 125 0 — 80 90 60 — 95 95 63 60 10 — 100 95 80 100 100 100 64 6010 30 90 60 — 100 100 100 65 125 20 — 80 80 80 — 95 95 66 125 0 — 100 —100 — 100 100 67 60 0 — 100 — 90 — 100 100 68 125 5 10 80 90 60 95 10095 70 60 10 — 90 90 — 90 100 100 72 125 10 — 90 70 — 95 100 100 76 60 030 95 — 95 — 100 95 77 60 0 — 95 — 90 — 100 90 80 125 0 — 95 — 90 — 10095 81 60 — — 100 — 95 — 100 100 82 60 0 — 60 — 90 — 100 100 84 125 5 3095 — 90 — 95 100 85 125 60 — 95 — 95 — 100 100 86 125 10 40 80 — 70 —100 95 89 125 0 — 100 — 90 — 100 100 93 60 0 — 90 — 80 — 95 90 108 125 5— 90 — 95 — 95 90 121 500 10 — 70 — 80 — 90 95 129 250 10 10 95 95 90 6090 95 130 250 10 0 95 95 80 95 95 95 131 250 0 0 95 90 90 95 80 95 134500 0 20 95 90 70 80 90 95 135 125 — 40 95 95 90 90 90 95 136 125 30 2095 95 90 80 90 95 140 30 — 10 — 95 95 80 80 95 141 15 30 0 90 80 80 9080 90 142 15 20 10 95 80 — 80 80 80 143 60 20 0 90 90 90 80 — 90 144 125— — 90 90 95 80 95 95 145 60 0 0 95 95 95 95 60 95 3 60 10 20 90 70 — 8095 80 146 60 0 10 80 90 — 80 80 90 147 15 30 0 95 90 — 70 70 80 148 6040 0 80 95 90 80 80 95 149 125 0 30 95 95 80 95 95 95 150 125 — 10 80 9080 70 80 80 151 15 20 10 90 90 50 80 90 90 152 125 — 20 95 95 95 95 8095 153 125 0 30 — 95 — 95 70 95 154 60 0 0 95 95 95 70 70 90 155 60 — 4095 95 95 90 80 95 156 60 0 10 70 90 70 70 95 70 157 60 0 20 90 80 80 95100 90 158 30 10 — 95 95 60 95 95 95 159 30 10 — 90 95 60 95 95 95 16060 30 10 90 90 60 90 95 90 161 60 0 20 95 95 — 95 95 95 162 60 — 0 95 9590 80 95 95 163 4 20 0 80 95 60 80 — 90 164 8 20 0 95 95 90 100 70 95165 8 0 10 — 90 70 80 90 80 166 15 40 — 90 90 70 80 95 90 167 60 — 30 8095 95 90 95 90 172 125 — 60 90 95 90 90 95 95

Example B

[0598] Post-emergence Test

[0599] Solvent: 5 parts by weight of acetone

[0600] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0601] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0602] Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the particularamounts of active compound desired are applied in 2000 1 of water/ha.

[0603] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0604] The figures denote:

[0605] 0%=no action (like untreated control)

[0606] 100%=total destruction

[0607] In this test, very strong activity against weeds is shown, forexample, by the compounds of Preparation Examples 1, 5, 6, 7, 28, 30,31, 32, 38, 44, 54, 63, 140, 141, 144, 151, 159, 162, 163, 164, 165 and166, combined with predominantly good tolerance by crop plants such as,for example, maize. TABLE B Post-emergence test/greenhouse Activecompound of Application Preparation rate Example (g of ai./ha) MaizeDigitaria Echinochloa Lolium Sorghum Amaranthus Gallium MatricariaStellaria 5 30 10 95 80 70 90 100 — 95 90 1 125 60 95 95 90 95 100 — 100100 6 400 20 90 95 95 80 100 90 100 100 7 60 15 95 95 95 100 — 95 95 10028 60 10 90 80 60 95 100 80 90 100 30 60 15 90 70 60 95 100 85 100 10031 30  5 95 95 90 80 100 80 100 95 32 60 70 70 100  70 95  95 70 80 9038 60 10 70 90 — 95 100 — 95 95 44 60 50 60 90 70 100 100 95 95 — 54 6030 — 95 95 95 100 85 100 100 63 60 — 50 90 70 80 100 90 95 100 140 250 —95 90 — 95 100 95 90 70 141 30 10 70 90 — 90 100 90 70 95 144 250 — 9595 70 95 100 95 70 95 151 30 60 90 70 60 90  95 90 90 90 159 60 — 60 8060 70  95 95 100 100 162 60 — 70 80 90 80 — — 60 90 163 60 60 80 70 8095 100 95 100 95 164 60 — 60 80 70 95 100 90 100 95 165 60 — 50 80 50 90 95 95 95 95 166 60 — 70 70 50 90  95 95 100 95

1. Substituted sulphonylamino(thio)carbonyl compounds of the generalformula (I),

in which A represents oxygen, sulphur, NH, N-alkyl, N-aryl, —CH═N—, or—N═CH— or —CH═CH—, Q represents oxygen or sulphur, R¹ representsrespectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, R²represents cyano, nitro, halogen or represents respectively optionallysubstituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl,alkylsulphonyl, alkenyl, alkinyl, alkenyloxy or alkinyloxy, and R³represents respectively optionally substituted heterocyclyl having 5ring members of which at least one represents oxygen, sulphur ornitrogen and a further one to three may represent nitrogen, and salts ofcompounds of the formula (I), except for the compoundsN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-oxazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-methyl-oxazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-4-ethyl-5-methyl-oxazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-ethyl-oxazole-4-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-ethyl-thiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-4-methylthio-thiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2,5-dimethyl-thiazole-4-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-2-chloro-thiazole-5-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-oxadiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-1,3,4-thiadiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-chloro-1,3,4-thiadiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-phenyl-1,3,4-thiadiazole-2-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-5-methyl-isoxazole-3-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-3-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-isoxazole-5-carboxamide,N-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-methyl-isoxazole-4-carboxamideandN-(2-chloro-6-methoxycarbonyl-phenylsulphonyl)-3,5-dimethyl-isoxazole-4-carboxamide.2. Compounds of the formula (I) according to claim 1, characterized inthat A represents oxygen, sulphur, NH, N-C₁-C₄-alkyl, N-phenyl, —CH═N—or —N═CH— or —CH═CH—, Q represents oxygen or sulphur, R¹ representsoptionally cyano-, nitro-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₆-alkyl, represents respectively optionally cyano- orhalogen-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, representsrespectively optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, represents respectivelyoptionally cyano-, nitro-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl orphenyl-C₁-C₄-alkyl, or represents respectively optionally cyano-,nitro-, halogen-, C₁ -C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁ -C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted heterocyclyl orheterocyclyl-C₁-C₄-alkyl, where in each case the heterocyclyl group isselected from the group consisting of oxetanyl, thietanyl, furyl,tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl,thiazolyl, oxadiazolyl, thiadiazolyl, R² represents cyano, nitro,halogen, represents respectively optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-carbonyl, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl orC₁-C₄-alkylsulphonyl, or represents respectively optionally cyano- orhalogen-substituted C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₂-C₄-alkenyloxy orC₂-C₄-alkinyloxy, and R³ represents respectively optionally substitutedheterocyclyl of the formulae below,

in which Q¹, Q² and Q³ each represent oxygen or sulphur and R⁴represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylidene-amino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, represents respectivelyoptionally fluorine-, chlorine- and/or bromine-substituted C₂-C₆-alkenylor C₂-C₆-alkinyl, represents respectively optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino orC₁-C₆-alkyl-carbonyl-amino, represents C₃-C₆-alkenyloxy, representsdi-(C₁-C₄-alkyl)-amino, represents respectively optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-amino orC₃-C₆-cycloalkyl-CI-C₄-alkyl, or represents respectively optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl- and/or C₁-C₄-alkoxy-substituted phenyl orphenyl-C₁-C₄-alkyl, R⁵ represents hydrogen, hydroxyl, mercapto, amino,cyano, fluorine, chlorine, bromine, iodine, represents optionallyfluorine-, chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl,represents espectively optionally fluorine-, chlorine- and/orbromine-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, representsrespectively optionally fluorine-, chlorine-, cyano-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, representsC₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio,C₃-C₆-alkinylthio, C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, representsdi-(C₁-C₄-alkyl)-amino, represents respectively optionally methyl-and/or ethyl-substituted aziridino, pyrrolidino, piperidino ormorpholino, represents respectively optionally fluorine-, chlorine-,bromine-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio,C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio or C₃-C6-cycloalkyl-C₁-C₄-alkylamino, or represents respectively optionallyfluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedphenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio,phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or R⁴and R⁵ together represent optionally branched alkanediyl having 3 to 11carbon atoms, furthermore R⁶, R⁷ and R⁸ are identical or different andeach represents hydrogen, cyano, fluorine, chlorine, bromine, orrepresents respectively optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy,alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl oralkylsulphonyl having in each case up to 6 carbon atoms or representoptionally cyano-, fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, and thesodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C4-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(CI-C4-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C2-alkyl)-benzyl-ammonium salts ofcompounds of the formula (I), except for the individual compoundsmentioned in claim
 1. 3. Compounds of the formula (I) according to claim1, characterized in that A represents sulphur, N-methyl, —CH═N— or—N═CH— or —CH═CH—, Q represents oxygen or sulphur, R¹ representsrespectively optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,represents respectively optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsrespectively optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclo-hexylmethyl, represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-,ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,phenylmethyl or phenylethyl, or represents respectively optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, methoxy- orethoxy-substituted heterocyclyl or heterocyclyl-methyl, where in eachcase the heterocyclyl group is selected from the group consisting ofoxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,R² represents cyano, fluorine, chlorine, bromine, representsrespectively optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or representsrespectively optionally cyano-, fluorine- or chlorine-substitutedpropenyl, butenyl, propinyl, butinyl, propenyloxy or propinyloxy, and R³represents respectively optionally substituted heterocyclyl of theformulae below,

in which Q¹, Q² and Q³ each represent oxygen or sulphur and R⁴represents hydrogen, hydroxyl, amino, represents respectively optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectivelyoptionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents respectively optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy or butenyloxy, represents dimethylamino or diethylamino,represents respectively optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents respectively optionally fluorine-,chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenylor benzyl, R⁵ represents hydrogen, hydroxyl, mercapto, amino, fluorine,chlorine, bromine, represents respectively optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents respectively optionallyfluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl,propinyl or butinyl, represents respectively optionally fluorine-,chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy,butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthiobutenylthio, propinylthio, butinylthio, propenylamino, butenylamino,propinylamino or butinylamino, represents dimethylamino, diethylamino ordipropylamino, represents respectively optionally fluorine-, chlorine-,methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentyl-methylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexyl-methylamino, or representsrespectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl-,methoxy- and/or methoxy-carbonyl-substituted phenyl, benzyl, phenoxy,benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or R⁴ andR⁵ together represent optionally branched alkanediyl having 3 to 11carbon atoms, furthermore R⁶, R⁷ and R⁸ are identical or different andeach represents hydrogen, cyano, fluorine, chlorine, bromine, orrepresents respectively optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloxy,butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, propenylthio, butenylthio, propinylthio, butinylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, orrepresents cyclopropyl, except for the individual compounds mentioned inclaim
 1. 4. Compounds of the formula (I) according to claim 1,characterized in that A represents sulphur or —CH═CH—, Q representsoxygen or sulphur, R¹ represents methyl, ethyl, n- or i-propyl,2-cyano-ethyl, 2-fluoro-ethyl, 2,2-difluoro-ethyl,2,2,2-trifluoro-ethyl, 2-chloro-ethyl, 2,2-dichloro-ethyl,2,2,2-trichloro-ethyl, 2-methoxy-ethyl, 2-ethoxy-ethyl or oxetanyl, R²represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,n-, i- or s-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy or trifluoroethoxy, and R³ representsoptionally substituted triazolinyl of the formula below

in which Q¹ represents oxygen or sulphur and R⁴ represents respectivelyoptionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, represents respectively optionally fluorine- orchlorine-subsituted propenyl or propinyl, represents methoxy, ethoxy, n-or i-propoxy, methylamino, ethylamino, n- or i-propylamino, representspropenyloxy, represents dimethylamino or represents cyclopropyl, R⁵represents chlorine or bromine, represents respectively optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectivelyoptionally fluorine-, chlorine- or bromine-substituted ethenyl,propenyl, butenyl, propinyl or butinyl, represents respectivelyoptionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-subsitutedmethoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representspropenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio,propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino,butenylamino, propinylamino or butinylamino, represents dimethylamino,diethylamino or dipropylamino, represents respectively optionallyfluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio,cyclobutylmethylthio, cyclopentyl-methylthio, cyclohexylmethylthio,cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino orcyclohexyl-methylamino, or represents respectively optionally fluorine-,chlorine-, methyl-, trifluoromethyl-, methoxy- and/ormethoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy,phenylthio, benzylthio, phenylamino or benzylamino, or R⁴ and R⁵together represent optionally branched alkanediyl having 3 to 11 carbonatoms.
 5. Process for preparing compounds of the formula (I) accordingto claim 1, characterized in that (a) sulphonarnides of the generalformula (II)

in which A, R¹ and R² are each as defined in claim 1, are reacted with(thio)carboxylic acid derivatives of the general formula (III)

in which Q and R³ are each as defined in claim 1 and Z representshalogen, alkoxy, aryloxy or arylalkoxy, if appropriate in the presenceof an acid acceptor and if appropriate in the presence of a diluent, orin that (b) sulphonyl iso(thio)cyanates of the general formula (IV)

in which A, Q, R¹ and R² are each as defined above, are reacted withheterocycles of the general formula (V) H—R³  (V) in which R³ is asdefined above, if appropriate in the presence of a reaction auxiliaryand if appropriate in the presence of a diluent, or in that (c)sulphonyl chlorides of the general formula (VI)

in which A, R¹ and R² are each as defined above, are reacted withheterocycles of the general formula (V) H—R³  (V) in which R³ is asdefined above, and metal (thio)cyanates of the general formula (VII)MQCN  (VII) in which Q is as defined above, if appropriate in thepresence of a reaction auxiliary and if appropriate in the presence of adiluent, or in that (d) sulphonyl chlorides of the general formula (VI)

in which A, R¹ and R² are each as defined above, are reacted with(thio)carboxamides of the general formula (VIII)

in which Q and R³ are each as defined above, if appropriate in thepresence of an acid acceptor and if appropriate in the presence of adiluent, or in that (e) sulphonylamino(thio)carbonyl compounds of thegeneral formula (IX)

in which A, Q, R¹ and R² are each as defined above and Z representshalogen, alkoxy, aryloXy or arylalkoxy, are reacted with heterocycles ofthe general formula (V) H—R³  (V) in which R³ is as defined above, ifappropriate in the presence of an acid acceptor and if appropriate inthe presence of a diluent, and the compounds of the formula (I) obtainedby processes (a), (b), (c), (d) or (e) are, if desired, converted intosalts by customary methods.
 6. Herbicidal composition, characterized inthat it contains at least one compound of the formula (I) or a saltthereof according to claim
 1. 7. The use of compounds of the generalformula (I) or of salts thereof according to claim I for controllingunwanted vegetation.
 8. Process for controlling weeds, characterized inthat compounds of the general formula (I) or salts thereof according toclaim 1 are allowed to act on the weeds or their habitat.
 9. Method forpreparing herbical compositions, characterized in that compounds of thegeneral formula (I) or salts thereof according to claim 1 are mixed withextenders and/or surfactants.
 10. Sulphonamides of the formula (IIa) andsulphonyl chlorides of the formula (VIa)

in which in each case R¹ represents respectively optionally substitutedalkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,heterocyclyl or heterocyclylalkyl and R² represents cyano, nitro,halogen or represents respectively optionally substituted alkyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl,alkinyl, alkenyloxy or alkinyloxy.